)urqwlhuv 7klvmrxuqdolv …c. shanghai engineering research center of molecular therapeutics and new...

1

Catalytic enantioselective synthesis of cyclopropanes featuring vicinal all-carbon quaternary stereocenters with a CH2F group; study of influence of C-F···H-N

interactions on reactivity

Zhong-Yan Cao,‡a Wenmin Wang,‡b Kui Liao,a Xiaoming Wang,d Jian Zhou*a,c,d and Jing Ma*b

aShanghai Key Laboratory of Green Chemistry and Chemical Process, East China Normal University, 3663N Zhongshan Road, Shanghai 200062, P. R. China. E-mail: jzhou@chem.ecnu.edu.cn. bInstitute of Theoretical and Computational Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, P R China. E-mail: majing@nju.edu.cn. cShanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, East China Normal University, 3663N Zhongshan Road, Shanghai 200062, P. R. China. dState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P R China. ‡These authors contributed equally to this article.

Supporting Information (Part C)

HPLC Spectra of 3a-3q, 4, 7a-7e 2-24

Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.This journal is © the Partner Organisations 2018

2

NNHH

OOCHCH22FF

nnBuBu

3a3a

NNHH

OOCCHH22FF

nnBBuu

33aa

3

NNHH

OOCCHH22FF

nnBBuu

MMee

33bb

NNHH

OOCHCH22FF

nnBuBu

MeMe

3b3b

4

NNHH

OOCCHH22FF

nnBBuu

FF

33cc

NNHH

OOCHCH22FF

nnBuBu

FF

3c3c

5

NNHH

OOCCHH22FF

nnBBuu

CCll

33dd

NNHH

OOCHCH22FF

nnBuBu

ClCl

3d3d

6

NNHH

OOCCHH22FF

nnBBuu

BBrr

33ee

NNHH

OOCHCH22FF

nnBuBu

BrBr

3e3e

7

NNHH

OOCCHH22FF

nnBBuu

II

33ff

NNHH

OOCHCH22FF

nnBuBu

II

3f3f

8

NNHH

OOCCHH22FF

nnBBuu

MMee33gg

NNHH

OOCHCH22FF

nnBuBu

MeMe3g3g

9

NNHH

OOCCHH22FF

nnBBuu

MMeeMMee

33hh

NNHH

OOCHCH22FF

nnBuBu

MeMeMeMe

3h3h

10

NNHH

OOCCHH22FF

CCll

CCll

33ii

NNHH

OOCHCH22FF

ClCl

ClCl

3i3i

11

NNHH

OOCCHH22FF

BBrr

CCll

33jj

NNHH

OOCHCH22FF

BrBr

ClCl

3j3j

12

NNHH

OOCCHH22FFCCll

MMee

33kk

NNHH

OOCHCH22FFClCl

MeMe

3k3k

13

NNHH

OOCCHH22FFCCll

33ll

NNHH

OOCHCH22FFClCl

3l3l

14

NNHH

OOCCHHFF22

nnBBuu

CCll

33mm

NNHH

OOCHFCHF22

nnBuBu

ClCl

3m3m

15

NNHH

OOCCHHFF22

nnBBuu

BBrr

33nn

NNHH

OOCHFCHF22

nnBuBu

BrBr

3n3n

16

NNHH

OOCCHHFF22

nnBBuu

II

33oo

NNHH

OOCHFCHF22

nnBuBu

II

3o3o

17

NNHH

OOCCHHFF22

OOMMee

BBrr

33pp

NNHH

OOCHFCHF22

OMeOMe

BrBr

3p3p

18

NNOOCCHH22FF

nnBBuu

MMee33qq

NNOOCHCH22FF

nnBuBu

MeMe3q3q

19

NNOO

CHCH22FF

nnBuBu

OO22SS NONO22

44

NNOO

CHCH22FF

nnBuBu

OO22SS NONO22

44

20

FFHH22CC CCOOOOMMee

PPMMPP

nnBBuu

77aa

FHFH22CC COOMeCOOMe

PMPPMP

nnBuBu

7a7a

21

FFHH22CC CCOOOOMMee

pp--BBrrCC66HH44

nnBBuu

77bb

FHFH22CC COOMeCOOMe

pp-BrC-BrC 66HH44

nnBuBu

7b7b

22

FFHH22CC CCOOOOMMee

mm--BBrrCC66HH44

nnBBuu

77cc

FHFH22CC COOMeCOOMe

mm-BrC-BrC66HH44

nnBuBu

7c7c

23

FFHH22CC CCOOOOMMee

pp--BBrrCC66HH44

77dd

FHFH22CC COOMeCOOMe

pp-BrC-BrC 66HH44

7d7d

24

FF22HHCC CCOOOOMMee

pp--BBrrCC66HH44

77ee

FF22HCHC COOMeCOOMe

pp-BrC-BrC 66HH44

7e7e